So I've been really struggling to understand the concept of "dilemma" vs "work" stories as defined by Dramatica. Specifically, how does story judgement factor into the evaluation of whether a story is one or the other?

To borrow the definition from the dramatica.com website:

APPARENT DILEMMA = CHANGE + FAILURE When a Main Character changes and the Overall Story Outcome is a failure, the audience believes that it only seemed like the Main Character should change, when in reality he shouldn't have.

Alright; sounds plausible at first pass. But this definition seems to fall apart when I apply it to failure/good stories. For example, To Kill a Mockingbird. This is a story with a change main character that ends in failure. So according to Dramatica terminology, TKAM would constitute an "apparent dilemma" story, where the Main Character should not have changed. But who would argue that Scout shouldn't have abandoned her prejudice against Boo Radley in the end of the novel?

APPARENT DILEMMA = CHANGE + FAILURE When a Main Character changes and the Overall Story Outcome is a failure, the audience believes that it only seemed like the Main Character should change in order to solve the story's problem (when in reality he shouldn't have).

The "should(/shoudn't)" relates to the story goal/problem, not the judgment. The issue with TKAM is that Scout has so little impact on the overall story of TKAM that saying "To solve the problem, Elliot should not have changed" is kind of nonsensical. It wouldn't have made any difference to the trial if she had remained steadfast. That's why I put the "shouldn't" in parenthesis. I like the idea that the story form only makes an argument about its argument, not anything else, i.e. if it's change/failure, it doesn't say anything about steadfast.

I'm with you @Audz -- I don't get the should vs. shouldn't terminology in that definition. Just because a Main Character Changed and a story ended in Failure, doesn't necessarily mean that remaining Steadfast would've resulted in Success. Or even if it's clear from the story that it would have, it's hard to apply "should" and "shouldn't" to the audience (a non-objective viewpoint) without considering Judgment.

Blade Runner is another good one to consider -- I don't think you can say that Deckard should've captured/killed all the replicants including Rachael.

Anyway, understanding this Audience Appreciation isn't crucial to working with Dramatica (either for analysis or for your own stories). I think it's okay to just think of stories by the individual points (Resolve, Outcome, Judgment).

But, definitely check out Jim's series (linked by @lovenote) if you haven't as that might help.

The responses here are great. It may sound like a copout but if you always come from the perspective of the storyform as an analogy to the mind's problem solving process then you'll be able to tell from time to time when the definitions are deficient in terms of that context.

In other words that definition approximates an understanding of outcome and resolve as seen from the audience point of view.